SA05260099B1 - مشتقات بيبريدين كمعدلات مستقبلة كيموكين ccr5 - Google Patents
مشتقات بيبريدين كمعدلات مستقبلة كيموكين ccr5 Download PDFInfo
- Publication number
- SA05260099B1 SA05260099B1 SA5260099A SA05260099A SA05260099B1 SA 05260099 B1 SA05260099 B1 SA 05260099B1 SA 5260099 A SA5260099 A SA 5260099A SA 05260099 A SA05260099 A SA 05260099A SA 05260099 B1 SA05260099 B1 SA 05260099B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- alkyl
- cia
- cis
- alkoxy
- optionally substituted
- Prior art date
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- 150000003053 piperidines Chemical class 0.000 title description 4
- 108700011778 CCR5 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 261
- 239000000203 mixture Substances 0.000 claims abstract description 192
- 238000000034 method Methods 0.000 claims abstract description 81
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 707
- 125000003545 alkoxy group Chemical group 0.000 claims description 137
- -1 alkenyl meth Chemical compound 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 79
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 60
- 238000006467 substitution reaction Methods 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000004927 fusion Effects 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 235000019506 cigar Nutrition 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 98
- 230000000694 effects Effects 0.000 abstract description 12
- 230000001105 regulatory effect Effects 0.000 abstract description 5
- 108010017088 CCR5 Receptors Proteins 0.000 abstract description 3
- 102000004274 CCR5 Receptors Human genes 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 339
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 170
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
- 239000000243 solution Substances 0.000 description 146
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 79
- 239000000047 product Substances 0.000 description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 229920000728 polyester Polymers 0.000 description 56
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
- 239000011541 reaction mixture Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 238000003756 stirring Methods 0.000 description 36
- 239000000377 silicon dioxide Substances 0.000 description 34
- 239000007787 solid Substances 0.000 description 32
- LXPRVXKHIXWBJZ-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CCl)C=C1 LXPRVXKHIXWBJZ-UHFFFAOYSA-N 0.000 description 31
- 239000003921 oil Substances 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- 239000000126 substance Substances 0.000 description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
- 239000000284 extract Substances 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 239000010410 layer Substances 0.000 description 22
- 206010039083 rhinitis Diseases 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 19
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 18
- 239000006260 foam Substances 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 238000004587 chromatography analysis Methods 0.000 description 17
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 16
- 239000012346 acetyl chloride Substances 0.000 description 16
- 201000010099 disease Diseases 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 16
- 108020003175 receptors Proteins 0.000 description 16
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- 208000006673 asthma Diseases 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 13
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 10
- 125000002883 imidazolyl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
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- 150000001721 carbon Chemical group 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 6
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- 239000005557 antagonist Substances 0.000 description 6
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
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SE0401057A SE0401057D0 (sv) | 2004-04-23 | 2004-04-23 | Chemical Compounds |
SE0500057A SE0500057D0 (sv) | 2005-01-10 | 2005-01-10 | Chemical compounds |
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SA5260099A SA05260099B1 (ar) | 2004-04-23 | 2005-04-20 | مشتقات بيبريدين كمعدلات مستقبلة كيموكين ccr5 |
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US (2) | US7615555B2 (ru) |
EP (1) | EP1742934A2 (ru) |
JP (1) | JP2007533735A (ru) |
KR (1) | KR20070007345A (ru) |
AR (1) | AR048834A1 (ru) |
AU (1) | AU2005235169B2 (ru) |
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TW (1) | TW200610761A (ru) |
UY (1) | UY28870A1 (ru) |
WO (1) | WO2005101989A2 (ru) |
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EP2066674B1 (en) * | 2006-09-18 | 2010-06-30 | F.Hoffmann-La Roche Ag | Octahydropyrrolo [3, 4-c] pyrrole derivatives and their use as antiviral agents |
TW200831483A (en) * | 2006-12-11 | 2008-08-01 | Astrazeneca Ab | Chemical compound |
TW200831093A (en) * | 2006-12-11 | 2008-08-01 | Astrazeneca Ab | Chemical compound |
AU2007334519A1 (en) * | 2006-12-14 | 2008-06-26 | Merck Sharp & Dohme Corp. | Acyl bipiperidinyl compounds, compositions containing such compounds and methods of treatment |
ES2536404T3 (es) * | 2007-02-23 | 2015-05-25 | K.H.S. Pharma Holding Gmbh | Procedimiento para la preparación de ésteres de azoniaspironortropina |
US7977358B2 (en) | 2007-07-26 | 2011-07-12 | Hoffmann-La Roche Inc. | Pyrazol derivatives |
WO2009126806A2 (en) | 2008-04-11 | 2009-10-15 | Janssen Pharmaceutica Nv | Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene a4 hydrolase |
US8217060B2 (en) | 2009-05-15 | 2012-07-10 | Janssen Pharmaceutica, Nv | Benzimidazole derivatives useful as TRP M8 receptor modulators |
EP2456309B1 (en) | 2009-07-24 | 2015-12-23 | GlaxoSmithKline LLC | Azabicyclo[3.2.1]octyl derivatives for use in the treatment of HIV. |
CN102241664B (zh) * | 2010-05-13 | 2014-11-12 | 上海医药工业研究院 | 芳烷二胺类衍生物及其作为抗抑郁症药物的应用 |
JP2013530947A (ja) | 2010-05-17 | 2013-08-01 | アレイ バイオファーマ、インコーポレイテッド | Gpr119調節薬としてのピペリジニル置換ラクタム |
US20140309226A1 (en) * | 2011-11-16 | 2014-10-16 | Array Biopharma Inc. | Piperidinyl-substituted cyclic ureas as gpr119 modulators |
JP6303250B2 (ja) | 2012-12-21 | 2018-04-04 | 石原産業株式会社 | 有害生物防除剤 |
WO2014102594A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
US10556899B2 (en) * | 2018-02-09 | 2020-02-11 | Sci Pharmtech, Inc. | Method for preparing Maraviroc |
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MX9100513A (es) | 1990-08-06 | 1992-04-01 | Smith Kline French Lab | Compuestos |
AU8576098A (en) | 1997-07-25 | 1999-02-16 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
AR013669A1 (es) * | 1997-10-07 | 2001-01-10 | Smithkline Beecham Corp | Compuestos y metodos |
WO1999025686A1 (en) * | 1997-11-18 | 1999-05-27 | Teijin Limited | Cyclic amine derivatives and their use as drugs |
JP2002501898A (ja) | 1998-02-02 | 2002-01-22 | メルク エンド カムパニー インコーポレーテッド | ケモカイン受容体活性の環状アミン調節剤 |
US6288083B1 (en) | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
US7217714B1 (en) * | 1998-12-23 | 2007-05-15 | Agouron Pharmaceuticals, Inc. | CCR5 modulators |
PE20001420A1 (es) * | 1998-12-23 | 2000-12-18 | Pfizer | Moduladores de ccr5 |
EP1013276A1 (en) | 1998-12-23 | 2000-06-28 | Pfizer Inc. | Aminoazacycloalkanes as CCR5 modulators |
SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
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KR100548854B1 (ko) | 2000-05-26 | 2006-02-02 | 화이자 인코포레이티드 | Ccr5 조절제로서의 트리아졸릴 트로판 유도체 |
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TW200610761A (en) | 2006-04-01 |
KR20070007345A (ko) | 2007-01-15 |
RU2368608C2 (ru) | 2009-09-27 |
AU2005235169A1 (en) | 2005-11-03 |
MXPA06012045A (es) | 2007-01-25 |
AR048834A1 (es) | 2006-05-31 |
EP1742934A2 (en) | 2007-01-17 |
US20070167442A1 (en) | 2007-07-19 |
UY28870A1 (es) | 2005-11-30 |
CA2562417A1 (en) | 2005-11-03 |
US7615555B2 (en) | 2009-11-10 |
WO2005101989A3 (en) | 2006-04-27 |
WO2005101989A2 (en) | 2005-11-03 |
IL178650A0 (en) | 2007-02-11 |
BRPI0510126A (pt) | 2007-06-26 |
US20100010007A1 (en) | 2010-01-14 |
AU2005235169B2 (en) | 2008-09-18 |
JP2007533735A (ja) | 2007-11-22 |
RU2006138663A (ru) | 2008-05-27 |
NO20065319L (no) | 2007-01-23 |
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